CA2049229A1 - Composition containing a polymer of unsaturated hydrocarbon, a c1-4 alkyl or hydroxyalkylether of starch and a vinyl or acryl polymer as a compatibilizing agent - Google Patents

Composition containing a polymer of unsaturated hydrocarbon, a c1-4 alkyl or hydroxyalkylether of starch and a vinyl or acryl polymer as a compatibilizing agent

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Publication number
CA2049229A1
CA2049229A1 CA002049229A CA2049229A CA2049229A1 CA 2049229 A1 CA2049229 A1 CA 2049229A1 CA 002049229 A CA002049229 A CA 002049229A CA 2049229 A CA2049229 A CA 2049229A CA 2049229 A1 CA2049229 A1 CA 2049229A1
Authority
CA
Canada
Prior art keywords
polymer
composition according
starch
weight
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002049229A
Other languages
French (fr)
Inventor
Henricus Eduard Hubertus Meijer
Anton Leendert German
Rita Maria Delrue
Antonius Hendrik Zijderveld
Jan Bussink
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cargill Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2049229A1 publication Critical patent/CA2049229A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/04—Starch derivatives, e.g. crosslinked derivatives
    • C08L3/08—Ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/053—Polyhydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/06—Polyethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C08L23/0869—Acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/06—Biodegradable
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/08—Polymer mixtures characterised by other features containing additives to improve the compatibility between two polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/06—Properties of polyethylene
    • C08L2207/066—LDPE (radical process)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond

Abstract

COMPOSITION CONTAINING A POLYMER OF UNSATURATED
HYDROCARBON, A C1-4 ALKYL OR HYDROXYALKYLETHER OF STARCH
AND A VINYL OR ACRYL POLYMER AS COMPATIBILIZING AGENT
Abstract of Disclosure A composition comprising a polymer of an unsaturated hydrocarbon, a C1-4 alkyl or hydroxyalkyl-ether of starch having a degree of substitution of at least 0.25, and a polyhydric aliphatic alcohol having 2 to 10 carbon atoms and 2 to 6 hydroxyl groups.

Description

S 6938~3 Can ~0~9~ 3 ~itle: ~sltl~ ~n~Alnlng a polyn~r o:t` urw~tu~t~ hy~a,r~l, a ~ 7r hyar~letbQr oi1 ~ar~ an~t a vi~l or a~ryl poly~r ~ ~ ~ti~illzir~ nt unsatu~t~ ~lr~car~, a Cl_4 all~l a~ 1~1~ O:e ~h h~vi~g a degree CR ~ at: l~t 0.25 ar~ a vl~yl or Ac~
p~ly~r as ~ cx~t~ izi~ ~nt.
I:lltCh pat~t a~?ll~icn ~902321, hhlct~ bll~ti-an, ~isclose~ a ~npo61itia~ ~1~ o~ltaln~ pol~n~ ~ ~s~tl~rDt~i hy-dr~a~on ar~ a Cl_4 al~l or hy~l)~ v;L~ ~ ~p~ of ~ub~tltu~ion o~ at l~t 0.~5 ~or iInpn~Vi~ ~ blo~bill1~y, ~xl bilizir~ , A v~r~l br ac:r~l ~lyme~ i~ u~
10 as the ~at~blliz~r~ agerlt, ~ partic~lar, a o~ly~ar o~ sthyle~a and vir~l ac:~tate (E~) or a oopolym~ o~ ylene ~ a~ryllc ~cid (EA7~).
y, a ~elati~,rely his~h ~nt~go ~ star~h ~iv~tlve Qn 3:~

p~tieular packa~i~ fil~ c~n be made. Aa~ ing to ~ tch appliea-15 tion it ~s pref~ to ~d ~ high~r Gar~lle ~eid, ~ ~s ~;t~ric:
aeid, oleie aeid or di~leie aeld, as a pla~tici2er or l~bricanl~, ~ald ear~71ie acid al~o a~ ~ t.
Accor~lil~ to this ir~ e present oc~6itiQn also cont~ns a pol~hydric ~lip}lati~ ol having 2-10 ca~orl atc~ ~rKI 2-fi h~-20 dro~yl ~u~s æ a disper~t/pl~sticizer/ll~bric~t for the star~he~her. ~he ~loo~ol has a bette~ di~sing action tlk~l the carbo~lic: -acid us~d in Dutch p~ pplication 8902321. me aloohol pr~rides bet-~er properties in tenns of ~3trength, ela~ticit:y a~ film fo~ming, ccq~
red to t~e use OL~ ~oxyllc acid as disc:lo~ ~n ~ appli~ion 25 ~902321.
D~-A-1,4~0,~6 dlsclose~ a co~bin~tlon o~ an alkyl or ~ ~ oxyalkyl st~rch ether, specific~lly a ~y~koxyethyl star~h ether or a hy~roxypro-pyl st3~h ether, havin~ the above-~entioned degree of substitu~ion, an alcohol s~ch as prGpylRne glycol, ~i~thylene gly~ol or ~yceri~e as a 30 plasticizer therefore, as ~ell as water Ln an AmLunt of 1-20% b~
weiqht. ~owever, ~lis reference ~es not m~ntion a hy~h~carbon polymer or any ot~r ~l~y~r ~ L~ ~sed in oombma~ion w~-th the starch ~erivati-ve,and thçrefore al~o a compatibili2ing agent is nct di~cl~ed. ~urther-~orç, in cont~dst to the pre~en~ appl~cation, wa~er has tD be pres~nt 35 aco~ding to this n~feren~e.

, ' 2 ~L9~ 3 qh~ late~ prw~ ~or pr~rln~ c~
position, a~3 wel~ a3 t4 pr~uc~t3 ~ich ~ve been m~de }~y ~r~f~ o~ thls cantEw~ or W~ 0~ ~id pr~.
Ag ~n ~ appllc:ation 8902321~ the poly~ o~ Un~sAtUl~ ~ hy~
5 drDc~a~on~3 ~ k~e u~d are in t~ i~ t pl~ lyole~ uch ~ the particular, athyl~ p~lyn~ ~ u~.
A~; in Dut~ a~llcatlc~ ~02321, the degr~ o~ ~ltutlon of 10 the ~:ther~ d 1~ ~t l~s~ 0.25 arxl pr~r~bly 0.4-l.o, ~hlle the pre~exre~ f~ e~erf~ are hy~roxypr~[~ th~, cd:)t;

~his re~ r~e, this aon~lens~ttion 13 p:ref~ly c~ d out usir~J
l~ne cataly1ls, in p~ lar with NaC~ ~y a ~tat~stic ~ trib 15 on o~ the pro~lucts ocx~urs.
As in ~h applicatiorl 8902321~ c~olymers o~ ethylene an~l vir~l acet~te (EVA) or o~ e~hylene and açrylic acid (E~A) are preee~ ly used a~; ccmpat~ilizin~ vinyl or acryl ~opolyn~s. E~rtl~re,te~polyn~ers of etl~lene, vi~l ~ ate ar~ (n~e~h)acrylic acld can be mentioned.
Exa~ple~ of the polyhydric alcchol t~3d in this inven~ion as dis-pirsan~plas~ er~lubrlcant are ~thylene glyc~l, pr ~ lene glycol, ~lyc~rine, butylene ylycol, d~ethylene ~lyool, pentaerythritol and d~-pentaer ~ itol. Ethylene glyc~l, prc~
pylene glycol a~ pen~erythritol are preferred,and of these c~n~x~nds 25 ethylene glycol ls m~6t pre~erre~.
The presen~ poly~ydric alc~hols are used ~ ~moun~s whi~ cause to swell or partlally dl~601ve the st~rch ether,and they æh~uld not be t~3d in such a large ~mcun~ that a ~ompl~te dissolution is achi~ved. For example,the preferred ~ydr~ypr~pyl starch diss~lves in ethylene gly401 30 in an amoun~ o~ 30% at 75'C and ~n propylen~ glycol in an amount of 40 %, while this ~ dissolv~s in glycerol in an amount of 10% at 100'~, Preferably,20-70~ ~y weight of pol~ of unsaturate~ hydrocar-bon, 20-~0% by we~h~ of starch ether, ll-19 % ky weight of cc~lpatibl-35 llzlng c~polymer an~ 2-8% by wei~h~ o~ polyhydric alcohol is u~ed ~n the ccmpc~it1On of this inv~ntion.
Because proces~in~ the mixtNre always mvolves a h~a~Lng ~tep, ~he polyhydric alcchol can ocmpletely develop it~ swelli~g or partially dis-solving action.

, 2 t~

A pre~ or pq~r~ th~ pres~ c~lticn~ pri-,Alth~ the l~v~rrtlon i~ n~ dependent on or r~trlct~
retl~ ~, lt ~ lisve4 l:l~t ~e hy~ger~ of the re d~Yn~ ~ ~e atheri~lcatlon, ~ter ~e pclyhyd~ic th~t th~ ~ partlcl~ Ar~ pre~t ~en~.y o~ . c~ a~
10 can ~e sub~ ally c~pl~tsly m~lex~ulnrly di~r~ed . ~n~ti~lead~ ~o CleAr ~d3 when the ~t~l et~r ~nd ~he polyhyclrio t~lccihol 'rha o~c~n o~ ir~ntic~n t~ ly ~i~l~ ~or the c~ oP ~ thr~d~lon~
15 re, starc~ ethe~3 and the polyhydri~ alco~ol ~d a~ he;.lp nkaterials, cheaper than the hydr~on pol~r. A perect o~osition conta~
50% of sta~ch e~her can ~e ~lbta~ned ea~;lly,aK~ also hlgher pen~ent~yes of star~ ether a~e ~t~ble. 0~ ~,the optima~ p~ent:age of ~tarc ether will al~o deperd ~n the u~;e of the oc~psition.
me ~ollctwing non-l~mitin~ e~ple illus~a~es ~s ~J~ention.

A m~ o$` S~ydro~propyl star~ hav~ a degree of s~tltution Or 0 5% and 10% by weight of ethyle~ glycol, ~ased on the st~r~l, was extr~ded at 75-C arxl alear bead~ were thus c~-t~ined~ 55 pa~s by w~
25 Or the bead~ were admixed with 15 par~s ~by weight of E~A an(:l 30 parts by weight of low densi~ 'chylene (LIDE~:~. Ihis mixhlre ~as extruded al,cl ~ilm~; were made. ~ e fi~ms had a tensile strength o~ ~.6 MPa/~n2 (a~ 50% o~ lue of ILDPE as such) and a yield value of 12.3,as c~ed to only 10.1 ~or polye~ylere as such. F~ hennore, the film ~0 s~ l~ation a~ brea~ of 330%. lhis ~bination of propertie~
ma)~es the ~:i~n c:Ju~s~ir~gly ~table a~ pa~g~ film, whic~ the additlonal advan~ge of }~eirg hiodegradable .
~;,3"~ II
xt~s A arr3 B, of linear luw pr~;s~re polyethylene (L~D~E), 35 hydroxyprc~pyl c,t~ (~æ) ~av.lng a degree of s~tit~ion of 0.5~6 and EAA (ethyler~e ac~yli~ ~c.id cc~polymer) as a c~mpatibilizir~ a~ent and stearic a~id were prep~re~. Ihe co~osltions oE the mi~ul~; are 13~r3ica-t~ le belc7w. ~.e mi~ were heA~ o 180~C ln an extruder and ex~rud~d to fo~m gr7~ate~; ar~ the granulat~,~re ~nade lnto ~ilms 2 ~ ~) F~rtl~re, 1;wo mix~,C ~ ~ v~ ~he ~ ccsnpo3itlon~ a) A, and B, r~ec~lvely, ~qpt tl~t the~;e n~x~ cor~tain~ 5 pa~t~ by w~l~h~
of gly~ol irlstead o~ 5 pa~ b~ wel~t o:~ ~ric z~ id, ~ prep S ~1 made into ~1~ acl:or~lr~ t4 th~ ~3 pr~.

t_ B ¦ C D

10 H~ 50 30 1 5~ 30 EAP~ 15 l~ 1 15 15 S~rlc acid 5 5 Gl~ 5 S
Terlail~ 5tr~r.g~h, MPa./~ l)1O-9 1 12.3 14.6 15 Elor~a~ion at ~r~c, ~6 _l) 360 ¦ 330 640 1) C~positi~n A ~ld r~t ba made into fil~ns .

Aç~ aEpe~ ~r~ ths above tablQ~ a~[ExN3~ki~n A, whic~ c~nt~
20 s~ ac!~d, oo~ld r~t be mad~ ~to flln~i, ~ile ca~3ition C, ~i~h ntic~al ~ a~itio~ A exc~ r ~ i~ac~ at C! c~r,ta~; glycol ~te~d o~ stearic ~cid, c~uld be made into filn~ h2~v~ desirable pr~
p~ies .
Co~osition O, ~ont~lnlr~ gly~o1, has a bett~ nce of pl~perti~;
2~ than c~mposi~ion B,whic~ di~ers fx~m campos~tian D in that I3 corltalns stearic ac:id ~nstead of ~lyc41.
~le III
5he foll~ 2 mixtures were prepared a~l made into fi~ns usir~
the method of ex~mple II. me H~S, EAA arx~ LI~PE were th~ 5~ as in th~
30 previou~; ex~ples.

, ::, :
: .

:~ ' :'' ~

2~922.~3 _ ~ ~r ~3ht ,__ Ethyl ~ glyc~
Glycarol - 5 E~A 15 15 J ~)PE 30 30 ~il~ ~h, MP~2 12.3 9 ~
Elor~lon at br~ 330 2~0.0 a~ C~po~ltian 1 ~ id~ttical ~ ~po~ lc~ C ln ~le II.

,

Claims (14)

1. A composition comprising a polymer of unsaturated hydrocarbon, a C1-4 alkyl or hydroxyalkyl ether of starch having a degree of substitution of at least 0.25 and a vinyl or acryl polymer as a compatibilizing agent, wherein the composition also contains a polyhydric aliphatic alcohol having 2-10 carbon atoms and 2-6 hydroxyl groups as a dispersant/plasticizer for the starch ether.
2. A composition according to claim 1, wherein the polyhydric alcohol is ethylene glycol, propylene glycol or glycerine.
3. A composition according to claim 1, wherein the hydrocarbon polymer is an ethylene polymer.
4. A composition according to claim 1, wherein the composition contains a condensation product of starch and propylene oxide as said starch ether.
5. A composition according to claim 1, wherein the starch ether has a degree of substitution of 0.4-1Ø
6. A composition according to claim 1, wherein the compatibilizing agent is a copolymer of ethylene and vinyl acetate or acrylic acid or a terpolymer of ethylene, vinyl acetate and acrylic acid.
7. A composition according to claim 1, wherein this composition contains polyethylene as said unsaturated hydrocarbon, hydroxy propyl starch as said starch ether, ethylene-acrylic acid copolymer as said compatibilizing agent and ethylene glycol as said alcohol.
8. A composition according to claim 7, wherein the composition contains linear low pressure polyethylene as said polyethylene.
9. A composition according to claim 1, wherein the composition contains 20-70% by weight of polymer of unsaturated hydrocarbon, 20-80% by weight of starch ether, 11-19% by weight of compatibilizing agent and 2-8% by weight of polyhydric alcohol.
10. A composition according to claim 7, wherein the starch ether has a degree of substitution of 0.4-1Ø
11. A composition according to claim 10, wherein said composition contains 20-70% by weight of polymer of unsaturated hydrocarbon, 20-80% by weight of starch ether, 11-19% by weight of compatibilizing agent and 2-8% by weight of polyhydric alcohol.
12. A process for preparing a composition according to claim 1, wherein the starch ether and the polyhydric alcohol are extruded together and thereafter the so-obtained homogeneous material is admixed with the other components and this mixture is extruded.
13. Articles, manufactured by means of a composition according to claim 1.
14. Articles, manufactured with the use of the process according to claim 13.

sd//
CA002049229A 1990-08-15 1991-08-15 Composition containing a polymer of unsaturated hydrocarbon, a c1-4 alkyl or hydroxyalkylether of starch and a vinyl or acryl polymer as a compatibilizing agent Abandoned CA2049229A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL9001826 1990-08-15
NL9001826A NL9001826A (en) 1990-08-15 1990-08-15 MATERIAL CONTAINING A POLYMER OF UNSATURATED HYDROCARBON, A C1-4 ALKYL OR HYDROXYALKYL ETHER OF STARCH AND A VINYL OR ACRYLIC POLYMER AS COMPATIBLE AGENT.
EP92200426A EP0561060B1 (en) 1990-08-15 1992-02-14 Composition containing a polymer of unsaturated hydrocarbons, a starch derivative and an ethylene butylacrylate copolymer

Publications (1)

Publication Number Publication Date
CA2049229A1 true CA2049229A1 (en) 1992-02-16

Family

ID=40316935

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002049229A Abandoned CA2049229A1 (en) 1990-08-15 1991-08-15 Composition containing a polymer of unsaturated hydrocarbon, a c1-4 alkyl or hydroxyalkylether of starch and a vinyl or acryl polymer as a compatibilizing agent

Country Status (11)

Country Link
US (1) US5234978A (en)
EP (2) EP0471402B1 (en)
AT (2) ATE129729T1 (en)
CA (1) CA2049229A1 (en)
DE (2) DE69114212T2 (en)
DK (2) DK0471402T3 (en)
ES (2) ES2080240T3 (en)
FI (2) FI913736A (en)
GR (1) GR3018678T3 (en)
NL (1) NL9001826A (en)
NO (1) NO180723C (en)

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DK0471402T3 (en) 1996-03-11
DE69225310D1 (en) 1998-06-04
EP0561060A1 (en) 1993-09-22
EP0471402A3 (en) 1992-04-15
FI930589A (en) 1993-08-15
DE69114212T2 (en) 1996-04-11
ES2080240T3 (en) 1996-02-01
FI913736A0 (en) 1991-08-06
ATE165612T1 (en) 1998-05-15
FI913736A (en) 1992-02-16
DE69225310T2 (en) 1998-08-20
NO180723C (en) 1997-06-04
NO913171D0 (en) 1991-08-14
EP0561060B1 (en) 1998-04-29
GR3018678T3 (en) 1996-04-30
NL9001826A (en) 1992-03-02
ES2118103T3 (en) 1998-09-16
FI930589A0 (en) 1993-02-11
NO913171L (en) 1992-02-17
DE69114212D1 (en) 1995-12-07
DK0561060T3 (en) 1998-10-07
NO180723B (en) 1997-02-24
EP0471402B1 (en) 1995-11-02
US5234978A (en) 1993-08-10
ATE129729T1 (en) 1995-11-15
EP0471402A2 (en) 1992-02-19

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